反应 #452429

反应方程式

hydrochloric acid

hexane

4-(4-fluorobenzoyl)aminophenylhydrazine

5-phthalimidyl-2-pentanone

hydrochloric acid

→

product

收率 6.6%

N-[2-methyl-3-(2-phthalimidylethyl)-1H-indol-5-yl]-4-fluoro-benzamide

收率 6.6%

溶剂

ethanol

反应条件

后处理

1. 1
   温度heating
2. 2
   温度The reaction mixture was then cooled to 0° C.
3. 3
   其他The solid which formed
4. 4
   过滤was filtered
5. 5
   洗涤washed with hexane
6. 6
   其他provided
7. 7
   其他after drying
8. 8
   浓缩The mother liquor was concentrated under reduced pressure
9. 9
   洗涤eluting with 1:1 hexane
10. 10
    workup.ADDITIONFractions containing product
11. 11
    浓缩concentrated under reduced pressure

实验过程

To a solution of 5.33 gm (21.7 mMol) 4-(4-fluorobenzoyl)aminophenylhydrazine and 5.03 gm (21.8 mMol) 5-phthalimidyl-2-pentanone in 100 mL ethanol were added 2 mL concentrated hydrochloric acid and the reaction mixture was heated at 80° C. for 14 hours. To the reaction mixture were then added an additional 3 mL concentrated hydrochloric acid and heating continued for an additional 6 hours. The reaction mixture was then cooled to 0° C. and 100 mL hexane were slowly added. The solid which formed was filtered and washed with hexane and provided, after drying, 6.67 gm of the desired compound. The mother liquor was concentrated under reduced pressure and then subjected to silica gel chromatography, eluting with 1:1 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide an additional 0.63 gm of product. Overall yield was 7.3 gm (76%).

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